[Hiring] Head of Engineering @SkillUp Coalition

Role Description

• Architecture & Technical Leadership:
  • Own platform architecture decisions across the full stack (MongoDB, APIs, Azure/GCP).
  • Establish technical standards and guide long-term platform evolution to support SkillUp's growth objectives.
  • Partner with the Head of Product to assess technical feasibility, identify trade-offs, and inform product roadmap decisions.
• Hands-On Software Development:
  • Maintain sufficient technical depth to provide architectural guidance and support critical initiatives.
  • Review complex implementations and contribute directly to the codebase when organizational needs require.
• Engineering Operations & DevOps:
  • Lead CI/CD pipelines, infrastructure-as-code, monitoring, and incident response.
  • Build and manage on-call rotation schedules ensuring platform reliability.
  • Own cloud infrastructure management across Azure and GCP.
  • Establish engineering processes that improve delivery predictability, operational excellence, and team effectiveness.
  • Establish engineering practices for AI observability, model monitoring, evaluation pipelines, and operational response to model degradation or hallucination risks.
  • Optimize infrastructure for performance and cost across cloud compute, vector databases, inference services, reporting systems, and AI workloads.
  • Develop CI/CD processes that support both traditional software deployments and AI model/prompt iteration.
• Security & Compliance:
  • Ensure security best practices across the platform, including data protection, access controls, vulnerability management, and responsible stewardship of sensitive user information.
• People & Vendor Leadership:
  • Lead, manage, and develop internal engineering staff and a near shore engineering team (engineers, QA, DevOps).
  • Foster growth, accountability, and a culture of collaboration, continuous learning, and inclusivity.
  • Develop engineering practices that support effective cross-functional partnership and sustainable team performance.
  • Manage Senior AI technical talent and external technical partners responsible for delivering secure, scalable AI product vision and capabilities in alignment with SkillUp’s product strategy.
• Product Partnership & Delivery Leadership:
  • Partner closely with the Head of Product to translate user and business needs into actionable engineering plans and delivery roadmaps.
  • Provide engineering perspectives to the CEO and leadership team on technical feasibility, scalability, sequencing, and resource requirements during roadmap planning.
  • Drive execution against agreed-upon priorities, balancing delivery speed with quality, maintainability, and platform sustainability.
  • Foster strong collaboration between engineering, product, design, analytics, and AI stakeholders to maximize user impact.
• AI Platform & Engineering Leadership:
  • Partner with the Head of Product and the engineering teams to build and scale SkillUp's AI-native career navigation platform.
  • Ensure AI capabilities are reliable, secure, observable, and production-ready.
  • Establish engineering patterns for integrating large language models (LLMs), AI agents, retrieval systems, orchestration frameworks, and structured data services into production applications.
  • Build the technical infrastructure necessary to evaluate, monitor, and continuously improve AI system performance.
  • Ensure AI services are architected with appropriate guardrails, testing strategies, human oversight, and responsible AI practices.
  • Develop engineering standards for prompt management, model versioning, experimentation, observability, and deployment across AI-powered services.

Qualifications

• 8+ years of professional software engineering experience, with 4+ years leading engineering teams and technical initiatives.
• Experience managing nearshore and/or contract engineering teams, including vendor relationships, SOWs, delivery oversight, and performance management.
• Experience partnering effectively with product leaders to deliver customer-facing technology solutions.
• Demonstrated ability to balance strategic technical thinking with hands-on execution in lean environments.
• Experience delivering AI-enabled or machine learning products into production, ideally leveraging LLMs, generative AI, agentic workflows, or intelligent automation.
• Familiarity with modern AI engineering patterns, including retrieval-augmented generation (RAG), vector databases, orchestration frameworks, prompt management, evaluation frameworks, and AI observability.
• Demonstrated ability to partner with AI engineers, data scientists, and product leaders to translate emerging AI capabilities into scalable customer experiences.
• Entrepreneurial mindset — comfortable navigating ambiguity, balancing competing priorities, and driving progress in resource-constrained environments.
• Dream Big, Get Sh*t Done, Know How to Have Fun.

Compensation & Benefits

• Target salary for this position is $175,000–$200,000, depending on experience, geography, and internal equity.
• SkillUp offers a generous compensation package which includes:
  • Employer-sponsored healthcare, vision and dental.
  • 401K employer match.
  • 25 days of office closure, PTO.
  • Education stipend.
  • Annual salary increases based on performance.